Using a food processor, in batches, pulse the oreos to a fine crumb.
In a mixing bowl, mix the oreo crumbs with butter, stir to combine.
Place oreo mixture into the bottom of a pre-greased 9x13 baking dish. Using your hands or the back of a measuring cup, pack the crumbs down so they hold together. Place in the refrigerator.
Next, using a large bowl, mix the cream cheese until smooth. Add half the powdered sugar, mix until well combined then add in the remaining powdered sugar, mixing until fully incorporated.
Add in 1 of the cool whip tubs and fold in with a spatula until mixed thoroughly. Place on top of the oreo mixture in an even layer and place back into the refrigerator.
Combine the chocolate pudding and milk, stir until smooth. Allow to thicken for 3-5 minutes before pouring over of the cream cheese mixture. Spread into an even layer.
Place the second tub of cool whip onto the chocolate pudding layer.
If desired, top with oreo crumbs.
Set in the refrigerator for 4 hours or overnight.